Synthesis and Characterization of Several Soluble Tetraphenoxy-Substituted Copper and Zinc Phthalocyanines

Chunyu Ma; Dongliang Tian; Xiaoke Hou; Yuchun Chang; Fangdi Cong; Haifeng Yu; Xiguang Du; Guotong Du

doi:10.1055/s-2005-861795

PAPER

Synthesis and Characterization of Several Soluble Tetraphenoxy-Substituted Copper and Zinc Phthalocyanines

Chunyu Ma^a, Dongliang Tian^c, Xiaoke Hou^b, Yuchun Chang^a,b, Fangdi Cong^c, Haifeng Yu^c, Xiguang Du*^c, Guotong Du*^a,b
^a Department of Physics, Dalian University of Technology, Dalian 116023, P. R. China
Fax: +86(411)4709304; e-Mail: bandaoti@mail.dlut.edu.cn; e-Mail: chunyu3ma76@yahoo.com.cn;
^b State Key Laboratory of Integrated Optoelectronics, Jilin University, Changchun 130021, P. R. China
^c Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China

Abstract

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Abstract

Synthesis of copper and zinc phthalocyanines (Pcs) bearing phenoxy-substituents is described. Precursors required for the preparation of Pcs 9-16 are prepared by a nucleophilic aromatic substitution reaction between a sterically hindered phenol derivative and 4-nitrophthalonitrile (1) or 3-nitrophthalonitrile (2). Cyclotetramerization of the resulting precursor phthalonitriles in DMAE or in pentan-1-ol catalyzed by DBU gives desired Pcs, which are well soluble in common organic solvents, such as chloroform and dichloromethane. Each of these Pcs are composed of four constitutional isomers and are characterized by ¹H NMR, UV/Vis, IR and mass spectra, as well as elemental analysis, which are consistent with the proposed structures.

Key words

phthalocyanines - zinc - copper - synthesis - phenols

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References

1 Maya EM. Garcia-Frutos EM. Vázquez P. Torres T. J. Phys. Chem. A. 2003, 107: 2110

2 Leznoff CC. Lever ABP. Properties and Application in Phthalocyanines Vol. 1-4: VCH; New York: 1989-1994.

3 Hanack M. Lang M. Adv. Mater. 1994, 6: 819

4 McKeown NB. Phthalocyanine Materials Cambridge University Press; Cambridge: 1998.

5 Kudrevich SV. Galpern MG. van Lier JE. Synthesis 1994, 779

6 Mitzel F. FitzGerald S. Beeby A. Faust R. Chem. Commun. 2001, 2596

7 Agirgtas MS. Bekaroglu O. J. Porphyrins Phthalocyanines 2001, 5: 717

8 Hanack M. Beck A. Lehmann H. Synthesis 1987, 703

9 McKeown NB. Chambrier I. Cook MJ. J. Chem. Soc., Perkin Trans. 1 1990, 1169

10 Leznoff CC. Marcuccio SM. Greenberg S. Lever ABP. Tomer KB. Can. J. Chem. 1985, 63: 623

11 Leznoff CC. Hu M. McArthur CR. Qin Y. van Lier JE. Can. J. Chem. 1994, 72: 1990

12 Merey S. Bekaroglu Ö. J. Chem. Soc., Dalton Trans. 1999, 4503

13 Sommerauer M. Rager C. Hanack M. J. Am. Chem. Soc. 1996, 118: 10085

14 Rager C. Schmid G. Hanack M. Chem. Eur. J. 1999, 5: 280

15 Snow AW. Jarvis NL. J. Am. Chem. Soc. 1984, 106: 4706

16 Dodsworth ES. Lever ABP. Seymour P. Leznoff CC. J. Phys. Chem. 1985, 89: 5698

17 Young JG. Williain O. J. Org. Chem. 1990, 55: 2155

18 Brewis M. Clarkson GJ. Humberstone P. Makhseed S. McKeown NB. Chem. Eur. J. 1998, 4: 1633

19 Hanack M. Meng DY. Beck A. Sommerauer M. Subramanian LR. J. Chem. Soc., Chem. Commun. 1993, 58

20 Hanack M. Schmid G. Sommerauer M. Angew. Chem., Int. Ed. Engl. 1993, 32: 1422 ; Angew. Chem. 1993, 105, 1540

21 Bolon DA. J. Am. Chem. Soc. 1966, 88: 3148

22 Montaudo G. Finocchiaro P. Trivellone E. Bottino F. Maravigna P. Tetrahedron 1971, 27: 2125

23 Bergman JJ. Chandler WJ. Can. J. Chem. 1972, 50: 353

24 Ong FD. Ning B. Du XG. Ma CY. Yu HF. Chen B. Dyes Pigm. in press

25 Kasuga K. Asano K. Lin L. Sugimori T. Handa M. Abe K. Kikkawa T. Fujiwara T. Bull. Chem. Soc. Jpn. 1997, 70: 1859

26 Kaneko Y. Arai T. Tokumaru K. Matsunaga D. Sakuragi H. Chem. Lett. 1996, 345

27 Yoon M. Cheon Y. Kim D. Photochem. Photobiol. 1993, 58: 31

28 Poon KW. Yan Y. Li XY. Ng DKP. Organometallics 1999, 18: 3528

29 Sastre A. Gouloumis A. Vázquez P. Torres T. Doan V. Schwartz BJ. Wudl F. Echegoyen L. Rivera J. Org. Lett. 1999, 1: 1807

30 Vacus J. Simon J. Adv. Mater. 1995, 7: 797

31 Argawal R. Athar M. Elmers CA. Bickers DA. Mukhtar H. Photochem. Photobiol. 1992, 56: 43

32 Sternberg ED. Dolphin D. Bruckner C. Tetrahedron 1998, 54: 4151